Holiday Rentals in Winona

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Winona

Charming ranch style log cabin with AC in scenic Winona
Private kitchen

Charming ranch style log cabin with AC in scenic Winona

10.0 out of 10, Exceptional, (1)
"First time staying in a cabin and was absolutely impressed! It was such a peaceful stay especially coming from being in the daily city life! David was awesome at communicating. Will be reserving again for sure!"
The price is €272
includes taxes & fees
8 Oct - 9 Oct
Charming ranch style log cabin with AC in scenic Winona
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Property grounds

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

10.0 out of 10, Exceptional, (1)
"This is a cute little rustic cabin. Chad was very friendly and open to suggestions due to being a first time host. "
The price is €162
includes taxes & fees
8 Oct - 9 Oct
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Charming 3-bedroom barn in quaint Winona with AC
Interior

Charming 3-bedroom barn in quaint Winona with AC

6.0 out of 10, (1)
"I had a hard time find this place, there need to be sign on old mountain road tell u how to get there. I had to clean one of the bathroom the shower was not clean. There are French door when u enter this place. There need to be some blind to the door."
The price is €382
includes taxes & fees
8 Oct - 9 Oct
Charming 3-bedroom barn in quaint Winona with AC
The most unique getaway experience in North Mississippi!
Exterior

The most unique getaway experience in North Mississippi!

10.0 out of 10, Exceptional, (4)
"The cabin was awesome, nicely laid out, large shower, and nice furnishings. The cabin is tranquil, and the view from the back porch, high up in the trees, is surreal. I have a daughter at Ole Miss, and I will be staying here throughout her college years if available"
The price is €262
includes taxes & fees
8 Oct - 9 Oct
The most unique getaway experience in North Mississippi!
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Fridge, microwave, oven, stovetop

4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

10.0 out of 10, Exceptional, (2)
"Amazing home and outdoor patio with pool! This place is beautiful and very close to Grenada Lake boat launch. "
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
Exterior

Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown

2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very nice stay, it’s the nicest house in the area! A lot of parking! "
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
Greenwood Studio Cottage < 1 Mi to Downtown!
Apartment (0 Bedroom) | Interior

Greenwood Studio Cottage < 1 Mi to Downtown!

3.5 star property
6.8 out of 10, (3)
"Every thing was great except the bed mattress was very uncomfortable, and the door to the bathroom was sticking when you open and closed it. Overall iitwas an excellent stay,"
Greenwood Studio Cottage < 1 Mi to Downtown!
Bream Shack-2 bedroom cabin with spacious parking
Interior

Bream Shack-2 bedroom cabin with spacious parking

8.4 out of 10, Very good, (5)
"Impeccable!"
The price is €285
includes taxes & fees
8 Oct - 9 Oct
Bream Shack-2 bedroom cabin with spacious parking
Cabin in the woods overlooking Grenada lake.
Dining

Cabin in the woods overlooking Grenada lake.

10.0 out of 10, Exceptional, (36)
"We enjoyed our stay!"
The price is €322
includes taxes & fees
8 Oct - 9 Oct
Cabin in the woods overlooking Grenada lake.
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
Terrace/patio

2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

10.0 out of 10, Exceptional, (1)
"THE CABIN WAS AMAZING!! THE VEIWS FROM THE BACK PORCH WAS ABSOLUTELY BREATH TAKING!THE CABIN WAS VERY NICE AND CLEAN. CAN'T WAIT TO GO BACK!"
The price is €216
includes taxes & fees
21 Oct - 22 Oct
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
Dogwoods-2 bedroom cabin with spacious parking
Fridge, microwave, oven, stovetop

Dogwoods-2 bedroom cabin with spacious parking

9.6 out of 10, Exceptional, (14)
"My family and I were in town for a family reunion, some other family members had stayed the previous year and highly recommend it. I was very impressed by the cleanliness of the cabin and the size was perfect for me and my family. The owners were very nice and even let us check in a little early. We visit that area a few times a year and if available we will definitely stay again. Thank You !"
The price is €233
includes taxes & fees
8 Oct - 9 Oct
Dogwoods-2 bedroom cabin with spacious parking
The Crappie-2 bedroom cabin with spacious parking
Exterior

The Crappie-2 bedroom cabin with spacious parking

10.0 out of 10, Exceptional, (5)
"Second time staying! GREAT HOST"
The price is €296
includes taxes & fees
8 Oct - 9 Oct
The Crappie-2 bedroom cabin with spacious parking
The Get-A-Way at Grenada lake
Fridge, microwave, oven, stovetop

The Get-A-Way at Grenada lake

9.8 out of 10, Exceptional, (12)
"Great place to stay for a fishing getaway ,close to the lake and not far from town . Owner was very responsive to my text , love that you can back your boats up under the shelter will definitely stay here again if we come down again!"
The price is €320
includes taxes & fees
8 Oct - 9 Oct
The Get-A-Way at Grenada lake
Homey Greenwood Getaway w/ Patio & Backyard
House (2 Bedrooms) | Interior

Homey Greenwood Getaway w/ Patio & Backyard

3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard
The Bass Shack-2 bedroom cabin w spacious parking
Interior

The Bass Shack-2 bedroom cabin w spacious parking

9.8 out of 10, Exceptional, (6)
"The cabin was a perfect place for a getaway or to stay and fish the lake. The property host was very accommodating and helpful with anything we needed. Highly recommend any of her properties, we will be back!"
The price is €285
includes taxes & fees
8 Oct - 9 Oct
The Bass Shack-2 bedroom cabin w spacious parking
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Fridge, microwave, oven, stovetop

5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

10.0 out of 10, Exceptional, (7)
"We came to Grenada to visit my wife's family. This was the perfect location and cabin for us. It's outside the city and a very peaceful setting. The barn was way more room than we needed. We enjoyed everything about it. "
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Charming family retreat
Outdoor dining

Charming family retreat

10.0 out of 10, Exceptional, (1)
"If u really wanted stay in the heart of greenwood it’s the perfect place to stay every thing about this house is perfect "
The price is €301
includes taxes & fees
14 Oct - 15 Oct
Charming family retreat
Secluded one bedroom cabin with large deck overlooking a wooded gully.
Interior

Secluded one bedroom cabin with large deck overlooking a wooded gully.

The price is €364
includes taxes & fees
8 Oct - 9 Oct
Secluded one bedroom cabin with large deck overlooking a wooded gully.
Located 3 miles to Grenada Lake
Fridge, microwave, oven, stovetop

Located 3 miles to Grenada Lake

10.0 out of 10, Exceptional, (1)
"Very Peaceful and relaxing "
Located 3 miles to Grenada Lake
Warm & Inviting home 5 minutes walking distance from restaurants.
Terrace/patio

Warm & Inviting home 5 minutes walking distance from restaurants.

9.2 out of 10, Wonderful, (5)
"Perfect for our family - 3 adults. Communication was tops, best we’ve ever had with VRBO."
Warm & Inviting home 5 minutes walking distance from restaurants.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winona Hotel Reviews

Comfort Inn & Suites Grenada

Comfort Inn & Suites Grenada

10/10 Excellent
"Safe parking around building and perimeter of the property. Room was clean and well supplied. Good variety of breakfast, as well as lemon water always available in the lobby. "
Julia 2-night trip
Posted 2 days ago
Comfort Inn & Suites Grenada

Find out more about Winona

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as €162 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay. Winona is known for its coffee shops and baseball games. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Winona has to offer?

Charming 3-bedroom barn in quaint Winona with AC: This highly rated holiday home rental in Winona has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Winona?

Take time out to visit local sights such as Montgomery County Performing Arts Center, Winona - Montgomery County Library, and Middleton Cemetery. Winona City Hall and Winona Country Club are other places to visit while you're in town.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip.